Nitromethane → 1-Chloro-3-fluoro-5-(2-nitroethenyl)benzene

HRID 20359Notes

Reaction equation

HRID 20359 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=O.[N+:11]([CH3:14])([O-:13])=[O:12].C([O-])(=O)C.[NH4+]>C(O)(=O)C.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:5]=[CH:14]/[N+:11]([O-:13])=[O:12])[CH:7]=[C:8]([F:10])[CH:9]=1

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 27348393-Chloro-5-fluorobenzaldehyde

Product 1

HCID 685627261-Chloro-3-fluoro-5-(2-nitroethenyl)benzeneYield 58.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 14798Sodium HydroxideSolvent

Procedure

Dissolve 3-chloro-5-fluorobenzaldehyde (4.0 g, 25.2 mmol) in glacial acetic acid (15 mL). Add nitromethane (4.1 mL, 75.7 mmol) and ammonium acetate (1.94 g, 25.2 mmol) and heat to reflux for 4 hours. Cool and pour over ice. Dilute with 2 N sodium hydroxide and extract with ethyl acetate, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 1:1 dichloromethane:hexanes) to give the desired compound as a beige solid (2.97 g, 58%).

Workup

  1. temperatureto reflux for 4 hours
  2. temperatureCool
  3. additionpour over ice
  4. extractionextract with ethyl acetate
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with 1:1 dichloromethane:hexanes)

Sources & evidence

ORD record
ord-235b4578a1404711aae4882b3e6e9455
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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